Shortening agent



Patented May 30, 1950 SHORTENING AGENT George Ban-sky, New York, N. Y,, assignor to E. F. Drew & Co. Inc., New York, N. Y., a corporation of Delaware No Drawing.

, Claims. 1

This invention is directed to shortening materials, more particularly, a shortening of the type wherein fatty acids are combined with glycerine.

A considerable number of years ago, it was proposed to use the monoand di-glycerides of higher fatty acids, particularly the fatty acids of'vegetable and animal oils of the glyceride type, as shortening materials in various baking processes. It has also been proposed to hydrogenate compounds of this character and add the same to an oil or fat whereby a mixture is obtained which is used for the same purpose. In compositions of this kind, the diglycerides have been stated to be inferior to the monoglycerides, on the basis that where there are two unesterifled hydroxy groups in each molecule, a higher efficiency for shortening purpose is obtained.

In accordance with the present invention it has been found that a shortening agent may be made containing the glycerides of fatty acids, but one in which the final products are substantially neutral triglycerides wherein all of the hydroxy groups of the glyceride molecules are substantially fully esterifled. Various advantages result from the use of agents of this type in baking processes.

In accordance with the present invention, there are first formed either mono or diglycerides of the higher fatty acids in a manner well known for a long time. The fatty acids used may be those of any of the common vegetable oils, such a cottonseed, soya bean, cocoanut, and the like,

or the oils themselves may be used to make the mono or diglycerides.

In general, those higher fatty acids having an even number of carbon atoms from 12 to 20 and occurring quite commonly in nature in various oils and fats, have been found most suitable for the present invention.

Such compounds have one or two of the hydroxy groups of each glycerinermolecule unesterifiecl or free. In accordance with the present invention, such compounds are reacted with an organic hydroxy acid of not over six carbon atoms, for instance, having the general formula RF-CHOH-COOH wherein R represents a hydrogen group or a hydrocarbon group having one to four carbon atoms. Therefore, the acids used in the present invention have from two to six carbon atoms in the molecule, and the OH group is attached to the a carbon atom.

A reaction is caused to occur between the glyceride and the hydroxy acid whereby all of the Application November 26, 1946, Serial No. 712,243

OH groups of the glyceride are substantially fully esterifled and a neutral product is obtained. Among the hydroxy acids which have been found quite suitable for the purpose are lactic acid and hydroxybutyric acid.

The structure of the compounds included in the present invention may be represented by the following structural formula- R(OH) 1&(CQOH) 10 wherein R. is a hydrocarbon radical having from 1 to 5 carbon atoms and n represents the numeral 1 or 2, the acids being water-soluble.

The following are specific examples of the production of mixed triglycerides, in accordance with the present invention, and adapted for use as shortening agents:

Example 1 1500 parts by weight of high quality oleic acid are mixed with 500 parts of 98% glycerine and the mixture is heated at 250 C. for about two hours while maintaining vigorous agitation of the mass. After the completion of the reaction, the mixture is then cooled and there is added thereto 958 parts of lactic acid containing approximately 15% of water. This mixture is gradually heated in high vacuum to a temperature of 180 C. over a period of three hours, and the temperature of the mixture is maintained at approximately this temperature for about two hours. This completes the formation of the triglyceride. The product is then treated in vacuo at 180 C. with a current of CO: to remove any free acid or glycerine.

The product is then mixed with usual shortening materials, such as oils or fats of vegetable or animalorigin, in the ratio of 1 part of the new reaction product to about 9 parts of the shortening material. This is accomplished by mixing the melted ingredients together, deodorizing, and then chilling on refrigerated rolls or other devices.

The resulting mixture may then be used for shortening purposes, as for example in the following formula for cake:

Grams Cake flour 812 Shortening 180 Granulated sugar 848 Baking powder 8.75 Salt 10.5 skimmed liquid milk 148 Egg whites Skimmed liquid milk 105 The composition containing the shortening of the present invention was baked at 350 F. for 1% hours. In order to obtain a comparison, a duplicate mixture was made using the usual shortening without the addition of the reaction product described above, the proportions of the ingredients being exactly the same as set forth above. The cake was baked under the same conditions. As a result, with the new shortening material a much larger volume of cake was obtained from the same amount of ingredients. The texture and grain thereof was superior to those of the upon current of carbon dioxide was blown through the mixture under vacumn until the-acid f This new com cake made with the ordinary shortening. With the prior art shortening, the cake was soggy and sticky while that formed with the present invention was uniformly attractive. The taste of the cake made with the present shortening was equal to that made with the prior art shortening under conditions more favorable for the prior art shortening.

Cakes were also made up with the following formula:

With this formula results with the shortening mixture of the present invention were greatly superior to those of the prior art shortening.

Example 2 A commercial vegetable oil shortening of the following properties was used:

Saponiflcation valu 196.2 FFA per cent .03 Iodine value 71.4 Wiley melting point F. 110.6 Congeal point C. 35.5

2824 parts of this shortening material was mixed with 707 parts of C. P. glycerine. This was heated to 435 F. in three hours with vigorous agitation. In three hours more it was heated to 470 F. It was held between 47049051. for 12 hours; all this was with vigorous agitation and with a reflux condenser to prevent escape of glycerine. The product was then cooled. It now had the following analysis:

Saponification value 168.5 FFA per cent-.. .55 Iodine value 58.6 Acetyl value 162.5

Distilled lactic acid. was prepared by vacuum distillation of commercial 50% lactic acid. This was done by removing the water under a vacuum of mm. After the water was removed the temperature was raised, and the fraction boiling at 131-180 C. at 8 mm. was collected. This fraction analyzed 102% lactic acid due to the presence content was reduced to .596 FFA. I position when added to ordinary shortening to,

theextent of about 10% produces an excellent cake whereas the ordinary shortening with the same cake formula does-not by itself yield an acceptable product.

I am aware that 'it has previously beenproposed to add lactic'acid and other acids such acetic to compositions used as substitutes-for butter. However, in such compositions the lactic acid was not a reactant and was not combined with any of the other ingredients, but the mixture contained free lactic acid, probably in give the composition a well deflned acidity. This was not for the purpose of improving the butter substitute as a shortening agent, but for other totally different purposes, mainly, in order togive the composition a desired taste which ordinarily might be lacking from the butter substitute. The

present invention contemplates a fully esterifled product wherein the hydroxy acid is combined with the glycerine molecule.

of som lactides. To 1200 parts of the reaction product of the glycerine and shortening oil, which comprised a mixture of tri-, monoand di-glycer ides, were added 500 parts of the concentrated 102% lactic acid. This was done by adding the lactic acid slowly to the heated oil at C. and 20 mm. vacuum. All the lactic acid was added over a period of 3% hours, after which the temperature was gradually raised to C; There- Although the invention has been described s'e ting forth several specific embodiments thereof, the invention is not limited thereto butvarious' modifications may e m de in the details thereof within the spirit of the invention. Other watersoluble carboxy acids maybe used in place of 1 the lactic acid set forth in the specific example.

Among the acids which are suitable for the pur pose are the following:

Glycolic acid, crno -cooH Sarcolactic acid. CHzCHOHCOOI-I Hydracrylic acid, CHzOHCI-IzCOOH Hydroxybutyric acid, cmoncmcmcoorr Y Malic acid, HOOC-CHOH-CHzCOOH Other acids .of similar character are also suitable; they may have odd or even numbers of carbon atoms and they may be straight chain or branched chain compounds.

When a hydroxy acid having more than one carboxy group is used for the utilization of the monoor di-glycerides, poly-esters are formed. These and other changes may be made in the details of the invention without departin from the principles set forth herein and the invention is therefor to be broadl construed and not to be limited except b the character of the claims appended hereto.

I claim:

1. A shortening agent comprising a glyceride oil having shortening properties, and the reaction 1 products of monoand diglycerides ofhlgher fatty acids of vegetable and animal oils with a water soluble acid having the general formulamonmcoomkwherein R represents hydrocarbon groups having from 1 to 5 carbon atoms, andm is 1 or 2, the

OH groups of the glycerine radicalbeing substantially fully esterifled.

2. A shortening agent comprising a glycerid oil having shortening properties, and the reaction products of mono and diglycerides of higher fatty acids of vegetable and animal oils with lactic acid; the OH groups of the glycerine being substantially full esterified.

"3. A shortening agent comprising a glyceride oil havingshortening properties, and the reaction productsof monoand diglycerids (if-higher fatty acids of vegetable oils and animal 5 hydroxybutyric acid, the OH groups of the g1yce:- ine being substantially fully esterified.

4. A shortening agent comprising a glyceride oil having shortening properties, and the reaction products of monoand diglycerides of oleic acid with a water soluble acid having the general formulawherein R represents hydrocarbon group havin from 1 to 5 carbon atoms, and n is 1 or 2, the OH groups of the glycerine radical being substantially fully esterifled.

5. A shortening agent comprising the reaction product of a substance taken from the class consisting of monoand di-glycerides of fatty acids having 12 to 20 carbon atoms, with a water soluble acid having the general formulawherein R represents hydrocarbon groups having from 1 to 5 carbon atoms, and n is 1 or 2.

6. The reaction product of a substance taken from the class consisting of monoand diglycerides of fatty acids having 12 to 20 carbon atoms, with a water soluble acid having the general formula-- RUOH) 11(COOH) 71 wherein R represents hydrocarbon groups having Irom 1 to 5 carbon atoms, and n is 1 or 2.

7. A shortening agent comprising a glyceride 6 oil having shortening properties, and the reaction products of monoand diglycerides of higher fatty acids of vegetable and animal oils with a water soluble acid having the general formula- R(OH) (COOH) REFERENCES CITED The following references are of record in the file of this patent:

UNITED STATES PATENTS Number Name Date 470,714 Sommer Mar. 15, 1892 1,505,550 Grun Aug. 19, 1924 1,547,571 Ellis H July 28, 1925 2,236,569 Grettie Apr. 1, 1941 2,266,591 Eckey Dec. 16, 1941 2,329,116 Tucker Sept. 7, 1943 V 

1. A SHORTENING AGENT COMPRISING A GLYCERIDE OIL HAVING SHORTENING PROPERTIES, AND THE REACTION PRODUCTS OF MONO- AND DIGLYCERIDES OF HIGHER FATTY ACIDS OF VEGETABLE AND ANIMAL OILS WITH A WATER SOLUBLE ACID HAVING THE GENERAL FORMULA- 